N-Alkanes to n-alcohols: Formal primary C-H bond hydroxymethylation via quadruple relay catalysis

Tang，Xinxin1; Gan，Lan1; Zhang，Xin1; Huang，Zheng1,2,3

2020-11-20

10.1126/sciadv.abc6688

Science Advances   影响因子和分区

2375-2548

2375-2548

Nature is able to synergistically combine multiple enzymes to conduct well-ordered biosynthetic transformations. Mimicking nature's multicatalysis in vitro may give rise to new chemical transformations via interplay of numerous molecular catalysts in one pot. The direct and selective conversion of abundant n-alkanes to valuable n-alcohols is a reaction with enormous potential applicability but has remained an unreached goal. Here, we show that a quadruple relay catalysis system involving three discrete transition metal catalysts enables selective synthesis of n-alcohols via n-alkane primary C-H bond hydroxymethylation. This one-pot multicatalysis system is composed of Ir-catalyzed alkane dehydrogenation, Rh-catalyzed olefin isomerization and hydroformylation, and Ru-catalyzed aldehyde hydrogenation. This system is further applied to synthesis of ?,?-diols from simple ?-olefins through terminal-selective hydroxymethylation of silyl alkanes.

SCI ; EI

英语

NI期刊

通讯

National Key R&D Program of China[2016YFA0202900] ; National Natural Science Foundation of China[21825109][21821002][21732006] ; Chinese Academy of Sciences[QYZDB-SSW-SLH016] ; Science and Technology Commission of Shanghai Municipality[17JC1401200]

Science & Technology - Other Topics

Multidisciplinary Sciences

WOS:000592173500025

AMER ASSOC ADVANCEMENT SCIENCE

20204909573433

Transition metals ; Catalysts ; Olefins ; Catalysis ; Hydrogenation

Metallurgy and Metallography:531 ; Chemical Reactions:802.2 ; Chemical Agents and Basic Industrial Chemicals:803 ; Chemical Products Generally:804 ; Organic Compounds:804.1

2-s2.0-85096814333

Scopus

1.State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,University of Chinese Academy of Sciences,Center for Excellence in Molecular Synthesis,Chinese Academy of Sciences,Shanghai,345 Lingling Road,200032,China
2.Shenzhen Grubbs Institute,Southern University of Science and Technology,Shenzhen,518055,China
3.Hangzhou Institute of Advanced Study,School of Chemistry and Material Sciences,University of Chinese Academy of Sciences,Hangzhou,1 Sublane Xiangshan,310024,China

Tang，Xinxin,Gan，Lan,Zhang，Xin,et al. N-Alkanes to n-alcohols: Formal primary C-H bond hydroxymethylation via quadruple relay catalysis[J]. Science Advances,2020,6(47).

Tang，Xinxin,Gan，Lan,Zhang，Xin,&Huang，Zheng.(2020).N-Alkanes to n-alcohols: Formal primary C-H bond hydroxymethylation via quadruple relay catalysis.Science Advances,6(47).

Tang，Xinxin,et al."N-Alkanes to n-alcohols: Formal primary C-H bond hydroxymethylation via quadruple relay catalysis".Science Advances 6.47(2020).